The Small Business Guide to Getting Ready for Vacation

Business Independencegetting ready for vacation

Getting ready for vacation is a challenge for many entrepreneurs and small business owners. A staggering 66% find it difficult to take time off, as per the June 2015 Office Depot Small Business Index.

Yet, taking a vacation is not only beneficial but essential for business health. It offers a chance to return recharged, with fresh ideas and a positive outlook, transforming overwhelming issues into manageable challenges.

A vacation also enriches your personal life, which often takes a backseat due to the demanding nature of running a business.

It’s a valuable opportunity to spend quality time with your family, strengthening bonds with your spouse and children and providing a well-deserved break from the rigors of business life.

Benefits of Taking Vacations as a Small Business Owner

Taking vacations while running a business might initially seem counterintuitive or even risky. After all, stepping away from daily operations can evoke fears of reduced productivity, overlooked details, or missed opportunities. However, the benefits of taking regular vacations for business owners far outweigh the perceived drawbacks. In fact, vacations can be instrumental in sustaining long-term success and personal well-being.

Vacations provide business owners a much-needed mental break from the relentless pace of entrepreneurship. This respite can lead to renewed energy, creativity, and motivation upon return. Furthermore, taking time off allows entrepreneurs to step back and assess their business’s trajectory from a distance, often leading to better strategic insights and decision-making. Importantly, vacations also signal trust in one’s team, allowing them to take charge in the leader’s absence, which can foster growth, responsibility, and improved morale within the organization.

Benefits of taking vacations while running a business include:

  • Mental Refreshment: A break from the daily grind rejuvenates the mind, reducing the risk of burnout.
  • Boosted Creativity: New environments and experiences can spark innovative ideas and solutions.
  • Improved Decision Making: Distance from daily operations allows for a broader perspective, leading to better strategic decisions.
  • Enhanced Employee Morale: Demonstrating trust in your team by allowing them to manage in your absence can boost their confidence and job satisfaction.
  • Personal Well-being: Vacations allow for quality time with loved ones, ensuring a balanced life outside work.
  • Reduced Stress: Disengaging from business pressures, even temporarily, can significantly reduce stress levels.
  • Increased Productivity: A rested mind is often more efficient, leading to better productivity upon return.

In summary, vacations are not just a luxury; they are a strategic necessity for business owners. While the immediate impulse might be to stay immersed in operations, regular breaks can lead to personal renewal and pivotal insights, both of which are vital for the long-term health and growth of a business.

Taking a vacation from business can be rejuvenating and beneficial, but the key to truly enjoying that time off lies in adequate preparation. Properly preparing for a vacation ensures that the business continues to run smoothly in the owner’s absence, mitigating potential issues or setbacks. By organizing tasks, communicating clearly with the team, and setting up contingency plans, business owners can prevent disruptions and enjoy their vacation with peace of mind.

A well-prepared vacation transition can also act as a testament to the efficiency and resilience of the business structure. It provides an opportunity for other team members to step up, take on leadership roles, and demonstrate their capabilities. Moreover, a smooth operational flow during the owner’s absence can boost client and stakeholder confidence, reassuring them of the company’s stability and professionalism.

Key steps to prepare before taking a vacation from business include:

  • Delegate Responsibilities: Identify key tasks and delegate them to trusted team members, ensuring they have the necessary resources and knowledge to execute them.
  • Clear Communication: Inform staff, clients, and stakeholders about the vacation in advance, so they are aware and can adjust their expectations or timelines if necessary.
  • Set Up an Emergency Contact: Even if you plan to disconnect, provide an emergency contact method or designate a point person for urgent issues.
  • Automate Where Possible: Utilize tools and software to automate tasks such as billing, email responses, or social media postings.
  • Document Procedures: Create or update documentation for standard procedures, ensuring that team members have a reference point in case of uncertainties.
  • Check Finances: Ensure that all bills, salaries, and financial obligations are taken care of or scheduled for payment.
  • Set Clear Expectations: Make sure the team understands their roles and responsibilities, and what is expected during the absence.
  • Prepare for Return: Organize a brief catch-up or review meeting for when you get back, so you can be updated on developments and address any pending issues.

The success of a vacation for a business owner isn’t just in the rest and relaxation they get, but also in the seamless continuity of business operations. Proper preparation not only ensures the company thrives in their absence but also allows the owner to genuinely disconnect and enjoy their well-deserved break.

Top Tips for Getting Ready for Vacation as a Small Business Owner

The trick to a worry-free vacation is proper planning. Follow these tips to get ready for vacation and you will soon be slipping into a pair of flip flops:

Preparation StrategyDescription / Key Points
1. Assign a Deputy- Designate a person to be in charge during your absence.
- Accept that mistakes might occur.
- If no managers, clearly define authority limits to employees.
2. Clear Your Plate- Avoid leaving unfinished projects.
- Work an extra hour or two in the lead-up to your vacation.
- Start with easy tasks to build momentum.
- Deliver projects early to maintain client trust.
3. Let People Know- Notify key contacts like clients about your vacation.
- Send reminders a few weeks and days before departure.
- Personal connections can be made when discussing plans.
4. Update Your Messages- Set up auto-reply email messages.
- Change voicemail to inform callers of your absence.
- Remember to revert to normal messages upon return.
5. Plan for Problems- Anticipate potential issues.
- Brief your team on how to handle various scenarios.
- Assure the team they can contact you for major issues.
6. Specify Emergency Numbers- Provide your personal contact for emergencies.
- List other contacts like insurance agents, attorneys, etc.
- Clarify preference between texts or calls.
7. Write Down Procedures- Document critical business procedures.
- Have employees practice procedures before you leave.
- Consider recording a video of critical tasks for reference.
8. Pay Your Bills- Ensure all upcoming bills are paid.
- Make arrangements for any bills or payroll that might come due during your vacation.
9. Clear Your Calendar- Check calendar for any upcoming events.
- Cancel or reschedule meetings and events that coincide with your vacation.
10. Don’t Be Available (Much)- Try to truly disconnect from work.
- If necessary, limit work-checking to a specific time slot daily.
11. Pack Light Tech- Opt for lighter tech options like tablets.
- Pre-download necessary apps.
- Use cloud storage or thumb drives for important documents.
12. Share The Memories- Share your vacation experiences briefly with the team.
- Consider bringing back small gifts for the team as a gesture of appreciation.

1. Assign a Deputy

getting ready for vacation

You’ll need someone to be in charge when you’re gone.

If you have managers in your company, they know their roles already. If you have more than one manager on your team and they are peers, it may help to designate one of them to be the main person in charge, in case of emergency.

Accept that mistakes will happen. Be sure your deputy knows he or she has your full confidence.

But what if you don’t have managers? That’s when you have to be clearer with your employees. They may need special instructions as to their authority and how far that authority extends. Make sure they know when to reach out to you.

  • Choose a trusted employee who understands the business well.
  • Clearly communicate their responsibilities and limits of their authority.
  • Provide training or guidance on any tasks they’re not familiar with.
  • Encourage team members to respect and support the deputy’s role in your absence.

2. Clear Your Plate

getting ready for vacation

You won’t like thinking about that stack of unfinished projects when you’re digging your toes in the sand, with sunscreen in one hand and a margarita in the other.

If you haven’t got a staff to delegate to when you’re inching out the door, here’s how to clear some of this stuff off your plate before you leave. Simply log an extra hour or two each day for a week or two in advance, whittling away those projects. That’s much better than pulling an all-nighter just before you’re due to drive 12 hours to the beach.

If you are a procrastinator, start with the easiest task first. Finish it — and the feeling of accomplishment may just get you fired up enough to tackle another project. And another.

Projects delivered before deadline make clients happy. And happy clients are less likely to fill your email box with missives or bug you by phone while you’re trying to decompress in paradise.

  • Prioritize tasks that need to be completed before your departure.
  • Delegate less critical tasks to team members.
  • Avoid taking on new major projects close to your vacation.
  • Set realistic goals for what can be achieved before you leave.

3. Let People Know

getting ready for vacation

Tell key people, such as clients and others who are used to dealing with you personally, that you’ll be away. It sets expectations. Knowing that, most people will not make urgent demands just before you leave.

Notify them a few weeks before your departure. Then provide another reminder a few days before you pack your bags. Here’s an example of a “going on vacation email” to send to clients and other key people:

“Just a short note to remind you that I will be on vacation  August 10 – 25, enjoying the sunny ocean at Myrtle Beach. For any product or service issues, Joe can assist you at [phone / email]. For anything else, please contact Mary in my absence at [phone / email].”

There’s another benefit to keeping clients in the loop. Discussing your vacation plans makes you a bit more human in their eyes. You’re no longer just the owner of a business. You and the other person may find you have a common interest in snorkeling, for example, and can better connect.

  • Notify clients, suppliers, and partners about your vacation plans well in advance.
  • Provide them with contact details of the person in charge during your absence.
  • Set an automated email responder and update your voicemail message to inform contacts of your unavailability.

4. Update Your Messages

getting ready for vacation

Some people like to create an auto-reply message for their email. That way, when a new email comes in, the sender gets an immediate response back that they’re out of the office. Simply adapt the message in Tip 3 above.

For Microsoft Office 365, set up the Automatic Replies feature. Or use the Rules and Templates functionality for Outlook desktop versions.

GMail and Google Apps email have an out-of-office reply feature that is easy to set up.

Don’t forget your voicemail, either. Consider leaving a recorded message alerting people that you’re out and will be returning messages more slowly than usual. Here’s a sample vacation voicemail message:

“Hi, this is [me]. Thanks for calling! I’m out of the office until [date]. If you have an urgent matter, please call Brittany at [number]. She will be glad to help.  Otherwise, please leave a message and I will get back to you when I return.”

Important: put a reminder in your calendar to swap out those messages as soon as you get back. Don’t be the person who still has that old vacation voicemail message playing weeks later.

  • Create a professional out-of-office email message detailing your absence and who to contact in emergencies.
  • Update your business’s social media status if necessary, to inform your audience about reduced responsiveness.
  • Ensure your emergency contact details are clearly mentioned in your out-of-office messages.

5. Plan for Problems

getting ready for vacation

Don’t automatically assume everything will go wrong in your absence — it won’t! But as you’re getting ready for vacation, do try to anticipate potential scenarios that might blow up.

Brief your team. Explain what you would do in each situation.

And assure them it’s okay to contact you if they feel the situation is beyond them. It’s better to interrupt your vacation for an hour, than to spend days fixing a mini disaster on your return.

  • Anticipate potential issues that could arise and prepare solutions.
  • Train your team on handling emergencies and when to escalate issues.
  • Leave detailed instructions for handling common problems.
  • Make sure your team knows how to reach you in case of a severe emergency.

6. Specify Emergency Numbers

getting ready for vacation

Make a list of two types of emergency numbers to give to key employees.

The first set of emergency numbers is your own, for employees who might need to reach you.

A mobile phone number is best. Give an alternate, too, just in case yours is turned off or the battery is dead — perhaps your spouse’s mobile phone.

Specify whether you want texts or calls. A short text message exchange can be less intrusive than a voice call, yet more immediate than email.

Next on the emergency contact list, designate people who may be able to answer questions in your absence. This list could include your business insurance agent, attorney or IT consultant.

  • Provide a list of contacts for different types of emergencies.
  • Include vendors, service providers, and other key contacts.
  • Make sure your team knows the protocol for using these emergency contacts.

7. Write Down Procedures

getting ready for vacation

Go over important business procedures that you will be delegating in your absence. For example, someone other than you may need to open the shop in the morning or close the office at night. Typical procedures that trip people up include:

  • setting the security alarm or turning it off in case it was accidentally triggered,
  • running credit card transactions,
  • processing payroll,
  • rebooting servers,
  • logging in as an admin to key software systems, or
  • anything the person is not used to handling.

Ask the employee to perform the procedures for you a couple of times before you leave.

Always write down the procedures as a backup, too. (Memory is a tricky thing.)

A quick video of you performing key procedures may be even better. Ask the employee to use his or her mobile phone to record it, so it can be a convenient refresher.

  • Document all critical business processes and procedures.
  • Include step-by-step guides for tasks your team might be unfamiliar with.
  • Store these documents in an easily accessible location.
  • Review these procedures with your team before leaving.

8.  Pay Your Bills

getting ready for vacation

Unpaid bills have a way of nagging and intruding in our minds. Who needs that?

Leave for your vacation with a clean slate of accounts payable. Pay invoices, credit card statements and bills that will come due while you’re gone. Make sure payroll is set up to be processed while you’re gone as well.

  • Schedule or automate payments for bills due during your vacation.
  • Review and reconcile accounts payable and receivable.
  • Ensure payroll is processed and scheduled in your absence.

9. Clear Your Calendar

getting ready for vacation

This might seem obvious, but the problem arises when people try to go by memory. Or they forget about recurring teleconferences and standing meetings that don’t appear on their calendar.

Actually check your calendar — before you leave. And take a moment to consciously think about those standing meetings and calls, so you can tell people not to expect you.

  • Reschedule meetings and appointments to after your return.
  • Decline new meeting requests for the duration of your vacation.
  • Check and double-check your calendar to ensure no commitments are overlooked.

10. Don’t Be Available (Much)

getting ready for vacation

Resist the temptation to take work with you. If you are glued to your laptop or phone, it not only will spoil your time but your family’s time, too. Imagine the grumpy faces of your family as they sit around waiting for you to get off the phone, so you can all go hiking.

Still, most business owners do want to stay in touch. They just don’t want to involve themselves so much that it stops feeling like a vacation. Seventy-six percent of business owners check their phones and email on vacation, according to the Office Depot Small Business Index survey.

If you must stay in touch with your business, limit it to a specific time slot each day. For example, you could set aside one half hour each morning at 9 a.m. to field messages that can’t wait or check in with staff. Once the 30 minutes are over, give yourself permission to go play with a clear conscience.

  • Set specific times for checking in on your business if necessary.
  • Communicate these check-in times to your team so they can consolidate updates or queries.
  • Resist the urge to constantly check emails or business updates.

11. Pack Light Tech

getting ready for vacation

Luckily, technology has made it easier than ever to stay in touch remotely. For those who don’t have staff, but still need to handle a few critical tasks while on vacation, mobile devices are a godsend.

A tablet or even a smartphone can substitute for a laptop while away. Just take the time to download a few key mobile apps in advance if you need to. A good app can make mobile transactions faster and easier.

Documents stored in the cloud can be accessed from a smartphone or tablet.  If you don’t use the cloud, take a few minutes before you leave to transfer critical files to a thumb drive.

  • Bring only essential tech gadgets needed to stay connected.
  • Download necessary apps and documents on your mobile devices before leaving.
  • Ensure remote access capabilities are set up and tested.

12. Share The Memories

getting ready for vacation

Remember:  a little R and R can bring some ROI (return on investment).

Upon your return, share your memories with your team for a few minutes. Not to bore them or make them feel bad that you were on vacation and they weren’t — but to reveal your human side. It strengthens staff relationships.

A nice touch is to bring something inexpensive back for team members, if practical. Boxes of saltwater taffy, T-shirts or coffee mugs all around show you thought about your team and you care.

  • Upon your return, take a few moments to share highlights from your vacation with your team.
  • Consider bringing back small souvenirs or treats as a gesture of appreciation.

Bonus Tip: Avoid The Social Media “Dead Giveaway”

It’s good planning to let “almost” everyone know you are leaving on vacation. But today there’s a big exception: social media sites. Here are some pointers for the security conscious:

  • Resist the urge to tell everyone on Facebook that you’ll be gone for two weeks. You don’t want to take the chance someone might break into your home — or your place of business if you don’t have a regular staff — while you’re away. Burglars have been known to monitor sites like Facebook.
  • Don’t use “check-in apps” such as Foursquare that show you at the airport or having dinner in a far-off place.
  • Avoid uploading fun family photos from some far off destination to Instagram or Twitter while you’re away. Save those photos and picturesque descriptions of that perfect beach on Maui until your return. The photos and the memories will keep. Your colleagues, clients, friends and extended family will love hearing about your adventures just as much when you’re safely back home again.
  • Adjust privacy settings on social media to control who sees your vacation posts.

Vacation Photo via Shutterstock

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Anita Campbell Anita Campbell is the Founder, CEO and Publisher of Small Business Trends and has been following trends in small businesses since 2003. She is the owner of BizSugar, a social media site for small businesses.

3 Reactions
  1. Hello, your bonus tip is one that everyone needs to take very seriously. Should you reveal your plans and current location on social media and then your premises gets broken into, you may find that just like domestic insurance, your insurer may refuse to pay out, considering you as an accessory to the crime.


  2. Yes. You must take a vacation every once in a while. It is better if you can do it with your employees. Just make sure that your operations are still intact. I always give the tasks to a friend who handles the same line of business. Though it is not advisable if you’re not really close because of competition.

  3. Great article! It’s so important for small business owners to take some time off and recharge their batteries. Vacations can indeed bring fresh perspectives and renewed energy, benefiting both the business and personal life.

    One additional point to consider is the importance of cybersecurity while you’re away. With the rise in cyber threats, it’s crucial to ensure that your business data and online presence are secure during your vacation. Consider using a virtual private network (VPN) to encrypt your internet connection and protect sensitive information while using public Wi-Fi. Also, make sure your cybersecurity measures are up to date and that you have a plan in place to respond to any potential security breaches.

    Enjoy your well-deserved vacation, and may it bring you the relaxation and inspiration you need for continued success in your business!

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